Planning your legacy is ultimately about stewardship — aligning money with meaning so family, causes, and commitments are cared for long after you’re gone. Below is a practical framework we use with clients to reduce avoidable friction, protect intent, and keep more of what you’ve built in the hands of people and purposes you choose. Because every situation is unique, you should decide on specific steps after consulting a qualified professional who can review your complete financial picture.

Set Up a Comprehensive Estate Plan

A thorough plan does more than distribute assets; it reduces delays and disputes, anticipates taxes, and gives your fiduciaries clear marching orders. At minimum, aim for:

Tax Signposts (2025–2026) You Should Know

Practical To‑Dos:

Identify and Address Potential Conflicts

Most estate blow‑ups aren’t about tax — they’re about people. Common pressure points:

  • Beneficiary designations that contradict the will or trust (remember: designations usually win).
  • Unequal (or “fair but not equal”) bequests among children or across blended families.
  • Illiquid assets (closely held businesses, real estate, collectibles) that are hard to split.
  • Roles and power dynamics: Who’s the executor, trustee, or business successor?

What helps:

Why this matters: Surveys repeatedly show family conflict is a leading source of estate plan failure — beneficiary designations and blended‑family issues often top the list.

Communicate with Your Beneficiaries

Silence can lead to suspicion. Even a brief, well‑structured conversation can head off years of conflict.

A simple agenda we use with families:

  1. Intent & values: Why does this plan exist, and what does a “good outcome” look like?
  2. Roles: Who does what—and why did you choose them (executor, trustee, health‑care agent)?
  3. What’s in scope: Overview of assets (not necessarily dollar amounts), liquidity sources (insurance, cash), and timetables.
  4. Ground rules: How disagreements are resolved and expectations for communication.
  5. Education: Explain the 10‑year timeline and potential annual RMDs under the new IRS rules to heirs inheriting retirement accounts.

When plans are openly discussed, heirs better understand the “why,” and you may dramatically reduce the likelihood of litigation or resentment later.

Review Regularly

Life (and law) changes. We recommend a check‑in every few years, and immediately after major events: marriage/divorce, births/deaths, relocation, liquidity events, buying/selling a business, large charitable commitments, or significant market moves.

What to watch now:

Why is This Urgent?

We are in the midst of the largest wealth transfer in U.S. history. Research projects $84.4 trillion moving through 2045 — most to heirs, with a meaningful share to charities. Planning determines how much of that supports your intent versus getting lost to taxes, delays, and disputes. 

How Grey Ledge Advisors Can Help

As fiduciaries, we coordinate the whole picture—investments, tax‑aware cash flows, trust funding, beneficiary alignment—and work side‑by‑side with your estate attorney and CPA so your documents, titling, and strategy sing from the same sheet of music. If you’d like, we can customize a one‑page action plan from this framework based on your family, assets, and state of residence.

More From Grey Ledge Advisors

Thanksgiving is a wonderful opportunity to get together with your family for a holiday that’s all about good food and gratitude. It can also be easily spoiled if conversations turn confrontational, which is why some subjects — namely politics and religion — are usually considered off-limits. 

Many people include financial matters on the list of off-limits topics during the holiday, but having the family together presents a perfect opportunity to discuss important financial matters — especially estate planning. While this may seem like an uncomfortable topic to bring up, effective communication with your loved ones is a critical part of the process. 

You don’t want this topic to come up by surprise, so give advance notice to your family that you’d like to make it part of the day. It doesn’t have to be the central discussion during the big meal; setting aside some time after the feast, or at some point during the long weekend, will suffice. 

Here are a few ways a family discussion about estate planning can be useful:

It helps set expectations

There has been considerable discussion about the massive wealth transfer that is expected to take place between Baby Boomers and younger generations. Fortune recently determined that the average Baby Boomer has a net worth of $970,000 to $1.2 million. An analysis by Cerulli and Associates estimates that the Baby Boomers and their parents (the Silent Generation) will pass on about $72.6 trillion to their Gen X and Millennial heirs.

This transfer of assets could have major ramifications for younger generations, especially for Millennials whose economic advancement has been hampered by challenges such as the Great Recession. Receiving a substantial sum could allow them to purchase a home, strengthen their retirement account, start an investment portfolio, or achieve other long-delayed financial goals.

However, there may also be a significant disconnect between what younger generations think they’ll inherit from their parents and what their parents are actually planning to leave them. While the figure in the Cerulli analysis is impressive, it’s worth noting that 42 percent of the wealth to be transferred is from ultra-high net worth households. A recent survey by Alliant Credit Union found that while 52 percent of Millennials believe they’ll receive an inheritance of at least $350,000, 55 percent of Baby Boomers said they were planning to leave less than $250,000 to their heirs.

Other factors also affect how much the older generations intend to leave for younger ones, or how much they’ll actually be able to pass on. Retirees must balance factors such as long-term care costs, higher costs due to inflation, and longer life expectancies to ensure that they don’t outlive their savings, and this can also limit how much money they’ll be able to pass on to their heirs.

A discussion about your finances can help set realistic expectations, and is also a good starting point for a conversation on estate planning. 

It gets the ball rolling

Failing to discuss what happens to a loved one’s assets after their death is a key source of wealth transfer problems. If you make your heirs aware of your plans and involve them in the process, it makes the process much smoother. 

An initial discussion on estate planning can simply inform your children of any plans and preparations you’ve made. Estate planning allows you to inventory all of your assets, including debts and liabilities, so you might share this information to help set expectations and discuss what you’d like to leave as an inheritance or as charitable donations. Your initial discussion can also be a useful way to inform your children about where your assets are being held, such as the names of any bank accounts, investment portfolios, and retirement accounts.

Clearly establish what steps you’ll be taking as part of your estate planning. This might include determining how your assets will be divided, setting up a will or a living trust, making preparations for long-term care, establishing health care directives, and setting up your power of attorney for financial and health care decisions in case you are incapacitated.

A Thanksgiving meeting is also a good way to get input from your offspring on your estate planning. You’ll be able to determine who is best suited to share the responsibility of this process, and make sure they’re ready for it. Your children may challenge some of your own assumptions as well; for example, you may believe that your family will want to keep a vacation home and discover in the course of the conversation that they’d prefer to sell it.

It can be the first in a series of important conversations

Estate planning is far too weighty a topic to cover in one conversation. While a discussion on Thanksgiving is a good starting point, you should regularly revisit the subject in the ensuing months and years.

Your initial talk might simply make a checklist of what you’re looking to accomplish as part of your estate planning, then make a plan for an ongoing dialogue. Perhaps you’ll want to set up weekly or monthly check-ins to keep your children up to date on your plans.

Financial advisors can help you prepare a family meeting to discuss your estate planning. These professionals will also take a considerable amount of stress off your children while also providing helpful expertise in organizing your assets, making sound investment decisions, and minimizing tax liabilities. They’ll also coordinate with attorneys overseeing the legal aspects of estate planning.